The gist of MG’s argument is that he’d rather work with people who are openly critical of his ideas if it helps him to perform better than to have a bunch of “yes men” around who just say what a great job he’s doing. I agree with that mentality. And the problem is that most people are “yes men” because it’s easier.

It’s far easier to tell somebody, “that looks great” than to defend why you don’t agree. To critique requires you to have your own point-of-view, to be able to articulate it and to be able to debate the merits of your point-of-view relative to the the other persons.

I have written about this topic in regards in different ways before and if you haven’t read them I think they’re probably both worth a glance:

When I sent out a Tweet with MG’s article I got a number of messages back saying the equivalent of “you don’t need to be a jerk to make a point. In today’s economy it is counter productive because the best employees have options.”

I agree with that sentiment (my motto is that life is too short to work with dicks) but I think it misses the point.

The broader message in my mind is one of being honest & direct with your feedback (= hard) versus giving people a free pass when you know something isn’t high quality (= easy).

I recently was reviewing a press release for a company in which I’m an investor. The CEO sent around his draft release to the entire investor base for comments. I would describe the responses at “atta boys” ranging from “awesome!” to “we’re so excited to work with you.”

My response?

I told him that I thought the press release was crap (I think my words, exactly). It was overly intellectual, had too many competing ideas, didn’t have enough catch phrases that would be picked up in the press, emphasized some facts that made us look smaller than we were, was too long and had terrible quotes.

I then asked for editing rights to his Google Doc and I rewrote a version of it. I then walked him through the logic of why I changed what I did. Of course I can’t write every press release for the company nor would I want to. I wanted to lead by example, make my points and then I hoped that the founder would think about how to do this himself the next time.

I promised him that if he liked his version better he could run with it and I wouldn’t complain. But that I was certain that my version was better for reasons a, b, c, d, e.

It was nearly 2am. Sure, it would have been ONE HELL OF A LOT EASIER to say, “well done! good luck!” but I cared more about the outcome and the lesson.

VC Pitches
I face this issue several times a week. I get presentations from aspiring entrepreneurs. Having been an entrepreneur for near-on a decade and having pitched in 100 VC meetings I hated getting no feedback. “Thanks, we’ll call ya” or “We really like you but need to see a bit more traction.”

So I swore when I got into the industry to provide real feedback, in real-time in my meetings.

I’m not always right. I say so.

I don’t live the business every day – you, do.

So if you have conviction and think I’m wrong – fine. I view my job is to be your sparring partner. To make sure you’ve thought methodically about your business. To pick hole’s in your approach. To try and save you wasted energy, help you avoid bad decisions and to make you that much better in your next VC meeting.

I try to do it constructively and with a smile on my face. But I can’t always be that. Sometimes I just serve it up directly. On a bad day I’m sure it can come off as condescending but I try my best not to make it so.

If I tell somebody that I am “absolutely certain this won’t work” (based on my judgment) I’m sure it doesn’t feel very nice. I usually try my best to offer constructive views on what they might do differently. But if my honest assessment is that they need a new CEO, need a better designed product, or similar – I will say so.

I subscribe to the philosophy that 70% of the people will respect me for my directness if I’m not a dick. They might not like the message at the time but later they may value the insights. 30% will likely just think I’m a dick. That’s OK.

I always believed that the job of a startup founder is to be Respected, Not Loved. And the same holds true for VCs. [if you never read that post, I think you’d enjoy it]

So if it takes 30% of the people to not like me in order to deliver some value to the 70% I’m willing to make that trade off.

It’s the harder path, trust me. You get argued with. You have to defend your point-of-view. It takes longer. You frustrate some people.

In Summary
I don’t believe in yelling at people. It’s counter productive. Don’t be a dick for dick’s sake. I’ve seen plenty of that in my career. But don’t give people a free pass on feedback. Take the harder track. Have a point-of-view. State it. Defend it. Push your colleagues (or your boss!) to produce higher quality work by challenging assumptions.

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2x startup Founder & CEO who has gone to the Dark Side of VC. His first company, BuildOnline was sold in 2005, his second, Koral was acquired by Salesforce.com and became known as Salesforce Content, while Mark served as VP Product Management. In 2007 Mark joined GRP Partners in 2007 as a General Partner. He focuses on early-stage technology companies, usually looking at Series A investment, and blogs at the aptly titled Both Sides of the Table.